Research Progress of Red Thermally Activated Delayed Fluorescent Materials Based on Quinoxaline

doi:10.6023/A21120587

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (3): 359-372.DOI: 10.6023/A21120587 Previous Articles Next Articles

Review

喹喔啉类红光热活化延迟荧光材料研究进展

周路, 陈嘉雄, 籍少敏, 陈文铖^*(), 霍延平^*()

广东工业大学轻工化工学院广州 510006

投稿日期:2021-12-27 发布日期:2022-02-08
通讯作者: 陈文铖, 霍延平

作者简介:

周路, 广东工业大学轻工化工学院2019级硕士研究生, 化学工程与技术专业. 主要从事有机发光材料的设计合成及其性能研究.

陈嘉雄, 广东工业大学化工与轻工学院副教授、硕士生导师, 有机光电材料与功能高分子团队骨干成员. 2010年获得广东工业大学学士学位, 并分别在汕头大学(2013年)和苏州大学(2018年)获得硕士和博士学位, 2018年~2021年在苏州大学能源学院从事博士后工作. 2018年~2021年在香港城市大学超金刚石及先进薄膜研究中心进行访问学习. 目前主要研究方向为有机光电功能材料及基于热活化延迟荧光材料的有机发光二极管.

陈文铖, 广东工业大学化工与轻工学院副教授、硕士生导师, 有机光电材料与功能高分子团队骨干成员. 2011年获得北京化工大学学士学位, 并分别在汕头大学(2014年)和香港城市大学(2018年)获得硕士和博士学位. 2018年5月~2019年11月在香港城市大学超金刚石及先进薄膜研究中心进行博士后研究. 目前研究方向主要包括有机光功能材料的设计合成及其在发光二极管、光学防伪与加密、生物医疗等领域的应用.

霍延平, 广东工业大学化工与轻工学院教授、博士生导师, 现任学院副院长, 有机光电材料与功能高分子团队负责人. 2006年获得中国科学院广州化学研究所博士学位. 广东省“千百十工程”省级培养对象、广东省有机化学专业委员会委员及国家自然科学基金通讯评审专家. 目前研究方向为有机电致发光材料和有机功能材料的绿色合成方法.

基金资助:
国家自然科学基金(52003058); 国家自然科学基金(U2001222); 国家自然科学基金(21975053); 国家自然科学基金(21975055); 国家自然科学基金(52003059); 广东省基础和应用基础研究基金(2019B1515120023); 广东省基础和应用基础研究基金(2019B1515120035); 广东省基础和应用基础研究基金(2021A1515010607); 广东省分子聚集发光重点实验室开放基金(2019-kllma-06)

Research Progress of Red Thermally Activated Delayed Fluorescent Materials Based on Quinoxaline

Lu Zhou, Jia-Xiong Chen, Shaomin Ji, Wen-Cheng Chen(), Yanping Huo()

School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006

Received:2021-12-27 Published:2022-02-08
Contact: Wen-Cheng Chen, Yanping Huo
Supported by:
National Natural Science Foundation of China(52003058); National Natural Science Foundation of China(U2001222); National Natural Science Foundation of China(21975053); National Natural Science Foundation of China(21975055); National Natural Science Foundation of China(52003059); Guangdong Basic and Applied Basic Research Foundation(2019B1515120023); Guangdong Basic and Applied Basic Research Foundation(2019B1515120035); Guangdong Basic and Applied Basic Research Foundation(2021A1515010607); Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates(2019-kllma-06)

Red emitter is one of the three primary materials for display, which is widely used in full-color display, biosensing and photodynamic therapy due to the advantages of small emission energy, strong penetrating ability and low background fluorescence interference. At present, the main bottlenecks for the development of red emitters are as follows. (1) The narrow energy gaps of red emitters often lead to serious non-radiative transition and low quantum efficiency. (2) The largely conjugated structure of red emitters results in strong π-π stacking for emission quenching. (3) Molecular design requires greater conjugation, which is difficult in molecular synthesis. Red thermally activated delayed fluorescence (TADF) materials, as a new type of red emitters, can use triplet excitons to release fluorescence through reverse intersystem crossing process, which greatly improves the quantum efficiency. Therefore, red TADF materials have become a hot topic in recent years. Because of the structural advantages, quinoxaline and its derivative are promising building blocks for the construction of red TADF emitters. The research progress of the quinoxaline-based red TADF materials in recent years is summarized, the influence of molecular structure on the properties of materials is discussed, and the prospect is also provided.

Key words: quinoxaline, red emission, thermally activated delayed fluorescence, organic light-emitting diode

Cite this article

Lu Zhou, Jia-Xiong Chen, Shaomin Ji, Wen-Cheng Chen, Yanping Huo. Research Progress of Red Thermally Activated Delayed Fluorescent Materials Based on Quinoxaline[J]. Acta Chimica Sinica, 2022, 80(3): 359-372.

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References 59

[1]	Forrest, S. R. Nature 2004, 428, 911. doi: 10.1038/nature02498
[2]	Luo, J.; Xie, G.; Gong, S.; Chen, T.; Yang, C. Chem. Commun. 2016, 52, 2292. doi: 10.1039/C5CC09797E
[3]	Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444. doi: 10.1002/adma.v29.22
[4]	Hong, G.; Gan, X.; Leonhardt, C.; Zhang, Z.; Seibert, J.; Busch, J. M.; Brase, S. Adv. Mater. 2021, 33, 2005630. doi: 10.1002/adma.v33.9
[5]	Cao, H.; Li, B.; Wan, J.; Yu, T.; Xie, L.; Sun, C.; Liu, Y.; Wang, J.; Huang, W. Acta Chim. Sinica 2020, 78, 680. (in Chinese) doi: 10.6023/A20030097
	曹洪涛, 李波, 万俊, 余涛, 解令海, 孙辰, 刘玉玉, 王锦, 黄维, 化学学报, 2020, 78, 680.) doi: 10.6023/A20030097
[6]	Liang, Z.-P.; Tang, R.; Qiu, Y.-C.; Wang, Y.; Lu, H.; Wu, Z.-G. Acta Chim. Sinica 2021, 79, 1401. (in Chinese) doi: 10.6023/A21070355
	(梁志鹏, 唐瑞, 邱雨晨, 王阳, 陆洪彬, 吴正光, 化学学报, 2021, 79, 1401.) doi: 10.6023/A21070355
[7]	Fang, F.; Zhu, L.; Li, M.; Song, Y.; Sun, M.; Zhao, D.; Zhang, J. Adv. Sci. 2021, 8, 2102970. doi: 10.1002/advs.v8.24
[8]	Fang, F.; Yuan, Y.; Wan, Y.; Li, J.; Song, Y.; Chen, W. C.; Zhao, D.; Chi, Y.; Li, M.; Lee, C. S. Small 2022, 18, 2106215. doi: 10.1002/smll.v18.6
[9]	Tang, C. W.; VanSlyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610. doi: 10.1063/1.343409
[10]	Leung, M.-K.; Chang, C.-C.; Wu, M.-H.; Chuang, K.-H.; Lee, J.-H.; Shieh, S.-J.; Lin, S.-C.; Chiu, C.-F. Org. Lett. 2006, 8, 2623. doi: 10.1021/ol060803c
[11]	Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikov, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 151. doi: 10.1038/25954
[12]	Qiu, Y.; Wei, P.; Zhang, D. Q.; Qiao, J.; Duan, L.; Li, Y. K.; Gao, Y. D.; Wang, L. D. Adv. Mater. 2006, 18, 1607. doi: 10.1002/(ISSN)1521-4095
[13]	Su, S.-J.; Gonmori, E.; Sasabe, H.; Kido, J. Adv. Mater. 2008, 20, 4189.
[14]	Tan, J.; Huo, Y.; Cai, N.; Ji, S.; Li, Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457. (in Chinese)
	(谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.) doi: 10.6023/cjoc201704015
[15]	Zhou, T.; Qian, Y.; Wang, H.; Feng, Q.; Xie, L.; Huang, W. Acta Chim. Sinica 2021, 79, 557. (in Chinese) doi: 10.6023/A21010009
	(周涛, 钱越, 王宏健, 冯全友, 解令海, 黄维, 化学学报, 2021, 79, 557.) doi: 10.6023/A21010009
[16]	Uoyama, H.; Goushi, K.; Shizu, K.; Nomura, H.; Adachi, C. Nature 2012, 492, 234. doi: 10.1038/nature11687
[17]	Endo, A.; Ogasawara, M.; Takahashi, A.; Yokoyama, D.; Kato, Y.; Adachi, C. Adv. Mater. 2009, 21, 4802. doi: 10.1002/adma.200900983
[18]	Chen, X. K.; Tsuchiya, Y.; Ishikawa, Y.; Zhong, C.; Adachi, C.; Bredas, J. L. Adv. Mater. 2017, 29, 1702767. doi: 10.1002/adma.v29.46
[19]	Ohsawa, T.; Sasabe, H.; Watanabe, T.; Nakao, K.; Komatsu, R.; Hayashi, Y.; Hayasaka, Y.; Kido, J. Adv. Opt. Mater. 2019, 7, 1801282. doi: 10.1002/adom.v7.5
[20]	Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931. doi: 10.1002/adma.v26.47
[21]	El-Sayed, M. A. J. Chem. Phys. 1963, 38, 2834. doi: 10.1063/1.1733610
[22]	Zhang, Q.; Kuwabara, H.; Potscavage, W. J. Jr.; Huang, S.; Hatae, Y.; Shibata, T.; Adachi, C. J. Am. Chem. Soc. 2014, 136, 18070. doi: 10.1021/ja510144h
[23]	Zeng, W.; Zhou, T.; Ning, W.; Zhong, C.; He, J.; Gong, S.; Xie, G.; Yang, C. Adv. Mater. 2019, 31, 1901404. doi: 10.1002/adma.v31.33
[24]	Zhao, J.; Yang, Z.; Chen, X.; Xie, Z.; Liu, T.; Chi, Z.; Yang, Z.; Zhang, Y.; Aldred, M. P.; Chi, Z. J. Mater. Chem. C 2018, 6, 4257. doi: 10.1039/C8TC01210E
[25]	Chen, S.; Dai, J.; Zhou, K.; Luo, Y.; Su, S.; Pu, X.; Huang, Y.; Lu, Z. Acta Chim. Sinica 2017, 75, 367 (in Chinese) doi: 10.6023/A17010015
	(陈仕琦, 代军, 周凯峰, 罗艳菊, 苏仕健, 蒲雪梅, 黄艳, 卢志云, 化学学报, 2017, 75, 367.) doi: 10.6023/A17010015
[26]	Lin, T. A.; Chatterjee, T.; Tsai, W. L.; Lee, W. K.; Wu, M. J.; Jiao, M.; Pan, K. C.; Yi, C. L.; Chung, C. L.; Wong, K. T.; Wu, C. C. Adv. Mater. 2016, 28, 6976. doi: 10.1002/adma.201601675
[27]	Zeng, W.; Lai, H. Y.; Lee, W. K.; Jiao, M.; Shiu, Y. J.; Zhong, C.; Gong, S.; Zhou, T.; Xie, G.; Sarma, M.; Wong, K. T.; Wu, C. C.; Yang, C. Adv. Mater. 2018, 30, 1704961. doi: 10.1002/adma.201704961
[28]	Wu, T.-L.; Huang, M.-J.; Lin, C.-C.; Huang, P.-Y.; Chou, T.-Y.; Chen-Cheng, R.-W.; Lin, H.-W.; Liu, R.-S.; Cheng, C.-H. Nat. Photonics 2018, 12, 235. doi: 10.1038/s41566-018-0112-9
[29]	Deol, H.; Singh, G.; Kumar, M.; Bhalla, V. J. Org. Chem. 2020, 85, 11080. doi: 10.1021/acs.joc.9b03407
[30]	Hogan, D. T.; Gelfand, B. S.; Spasyuk, D. M.; Sutherland, T. C. Mater. Chem. Front. 2020, 4, 268. doi: 10.1039/C9QM00710E
[31]	Oliveira, P. F. M.; Haruta, N.; Chamayou, A.; Guidetti, B.; Baltas, M.; Tanaka, K.; Sato, T.; Baron, M. Tetrahedron 2017, 73, 2305. doi: 10.1016/j.tet.2017.03.014
[32]	Hussain, H.; Specht, S.; Sarite, S. R.; Saeftel, M.; Hoerauf, A.; Schulz, B.; Krohn, K. J. Med. Chem. 2011, 54, 4913. doi: 10.1021/jm200302d
[33]	Zhang, Y.; Zhang, D.; Cai, M.; Li, Y.; Zhang, D.; Qiu, Y.; Duan, L. Nanotechnology 2016, 27, 094001. doi: 10.1088/0957-4484/27/9/094001
[34]	Wang, S.; Yan, X.; Cheng, Z.; Zhang, H.; Liu, Y.; Wang, Y. Angew. Chem., Int. Ed. 2015, 54, 13068. doi: 10.1002/anie.v54.44
[35]	Wang, S.; Cheng, Z.; Song, X.; Yan, X.; Ye, K.; Liu, Y.; Yang, G.; Wang, Y. ACS Appl. Mater. Interfaces 2017, 9, 9892. doi: 10.1021/acsami.6b14796
[36]	Furue, R.; Matsuo, K.; Ashikari, Y.; Ooka, H.; Amanokura, N.; Yasuda, T. Adv. Opt. Mater. 2018, 6, 1701147. doi: 10.1002/adom.201701147
[37]	Wang, S.; Miao, Y.; Yan, X.; Ye, K.; Wang, Y. J. Mater. Chem. C 2018, 6, 6698. doi: 10.1039/C8TC01746H
[38]	Xie, F. M.; Wu, P.; Zou, S. J.; Li, Y. Q.; Cheng, T.; Xie, M.; Tang, J. X.; Zhao, X. Adv. Electron. Mater. 2019, 6, 1900843. doi: 10.1002/aelm.v6.1
[39]	Zhang, Y. L.; Ran, Q.; Wang, Q.; Liu, Y.; Hanisch, C.; Reineke, S.; Fan, J.; Liao, L. S. Adv. Mater. 2019, 31, 1902368. doi: 10.1002/adma.v31.42
[40]	Balijapalli, U.; Nagata, R.; Yamada, N.; Nakanotani, H.; Tanaka, M.; D'Aleo, A.; Placide, V.; Mamada, M.; Tsuchiya, Y.; Adachi, C. Angew. Chem., Int. Ed. 2021, 60, 8477. doi: 10.1002/anie.v60.15
[41]	Liu, Y.; Chen, Y.; Li, H.; Wang, S.; Wu, X.; Tong, H.; Wang, L. ACS Appl. Mater. Interfaces 2020, 12, 30652. doi: 10.1021/acsami.0c07906
[42]	Chen, J. X.; Wang, K.; Zheng, C. J.; Zhang, M.; Shi, Y. Z.; Tao, S. L.; Lin, H.; Liu, W.; Tao, W. W.; Ou, X. M.; Zhang, X. H. Adv. Sci. 2018, 5, 1800436. doi: 10.1002/advs.201800436
[43]	Chen, J. X.; Tao, W. W.; Chen, W. C.; Xiao, Y. F.; Wang, K.; Cao, C.; Yu, J.; Li, S.; Geng, F. X.; Adachi, C.; Lee, C. S.; Zhang, X. H. Angew. Chem., Int. Ed. 2019, 58, 14660. doi: 10.1002/anie.v58.41
[44]	Chen, J. X.; Xiao, Y. F.; Wang, K.; Sun, D.; Fan, X. C.; Zhang, X.; Zhang, M.; Shi, Y. Z.; Yu, J.; Geng, F. X.; Lee, C. S.; Zhang, X. H. Angew. Chem., Int. Ed. 2021, 60, 2478. doi: 10.1002/anie.v60.5
[45]	Yuan, Y.; Hu, Y.; Zhang, Y.-X.; Lin, J.-D.; Wang, Y.-K.; Jiang, Z.-Q.; Liao, L.-S.; Lee, S.-T. Adv. Funct. Mater. 2017, 27, 1700986. doi: 10.1002/adfm.v27.26
[46]	Yu, Y. J.; Hu, Y.; Yang, S. Y.; Luo, W.; Yuan, Y.; Peng, C. C.; Liu, J. F.; Khan, A.; Jiang, Z. Q.; Liao, L. S. Angew. Chem., Int. Ed. 2020, 59, 21578. doi: 10.1002/anie.v59.48
[47]	Xue, J.; Liang, Q.; Wang, R.; Hou, J.; Li, W.; Peng, Q.; Shuai, Z.; Qiao, J. Adv. Mater. 2019, 31, 1808242. doi: 10.1002/adma.v31.28
[48]	Gong, X.; Li, P.; Huang, Y. H.; Wang, C. Y.; Lu, C. H.; Lee, W. K.; Zhong, C.; Chen, Z.; Ning, W.; Wu, C. C.; Gong, S.; Yang, C. Adv. Funct. Mater. 2020, 30, 1908839. doi: 10.1002/adfm.v30.16
[49]	Gong, X.; Lu, C.-H.; Lee, W.-K.; Li, P.; Huang, Y.-H.; Chen, Z.; Zhan, L.; Wu, C.-C.; Gong, S.; Yang, C. Chem. Eng. J. 2021, 405, 126663. doi: 10.1016/j.cej.2020.126663
[50]	Hu, X.; Zhong, C.; Li, X.; Jia, X.; Wei, Y.; Xie, L. Acta Chim. Sinica 2021, 79, 953. (in Chinese) doi: 10.6023/A21050196
	(胡鑫明, 钟春晓, 李晓艳, 贾雄, 魏颖, 解令海, 化学学报, 2021, 79, 953.) doi: 10.6023/A21050196
[51]	Yuan, Y.; Chen, J.-X.; Lu, F.; Tong, Q.-X.; Yang, Q.-D.; Mo, H.-W.; Ng, T.-W.; Wong, F.-L.; Guo, Z.-Q.; Ye, J.; Chen, Z.; Zhang, X.-H.; Lee, C.-S. Chem. Mater. 2013, 25, 4957. doi: 10.1021/cm4030414
[52]	Yuan, Y.; Chen, J.-X.; Chen, W.-C.; Ni, S.-F.; Wei, H.-X.; Ye, J.; Wong, F.-L.; Zhou, Z.-W.; Tong, Q.-X.; Lee, C.-S. Org. Electron. 2015, 18, 61. doi: 10.1016/j.orgel.2015.01.009
[53]	Cai, Z.; Wu, X.; Liu, H.; Guo, J.; Yang, D.; Ma, D.; Zhao, Z.; Tang, B. Z. Angew. Chem., Int. Ed. 2021, 60, 23635. doi: 10.1002/anie.v60.44
[54]	Zhao, B.; Wang, H.; Han, C.; Ma, P.; Li, Z.; Chang, P.; Xu, H. Angew. Chem., Int. Ed. 2020, 59, 19042. doi: 10.1002/anie.v59.43
[55]	Yu, H.; Song, X.; Xie, N.; Wang, J.; Li, C.; Wang, Y. Adv. Funct. Mater. 2020, 31, 2007511. doi: 10.1002/adfm.v31.5
[56]	Li, C.; Duan, R.; Liang, B.; Han, G.; Wang, S.; Ye, K.; Liu, Y.; Yi, Y.; Wang, Y. Angew. Chem., nt. Ed. 2017, 56, 11525.
[57]	Li, Z.; Yang, D.; Han, C.; Zhao, B.; Wang, H.; Man, Y.; Ma, P.; Chang, P.; Ma, D.; Xu, H. Angew. Chem., nt. Ed. 2021, 60, 14846.
[58]	Yang, T.; Liang, B.; Cheng, Z.; Li, C.; Lu, G.; Wang, Y. J. Phys. Chem. C 2019, 123, 18585. doi: 10.1021/acs.jpcc.9b05875
[59]	Yang, T.; Cheng, Z.; Li, Z.; Liang, J.; Xu, Y.; Li, C.; Wang, Y. Adv. Funct. Mater. 2020, 30, 2002681. doi: 10.1002/adfm.v30.34

Emitter		λ_PL/nm		Φ_PL/%		τ_DF/μs		ΔE_ST/eV		Host (emitter, w)		λ_EL/nm		EQE/%	CIE (x, y)		Ref
1		588^a/708^b		84^a/14^b		0.76^b		0.13		Nondoped/TPBi (20%)		710/668		2.1/9.8	0.70, 0.29/0.68, 0.32		[34]
2		531^a/560^c		88^a/61^c		130^c		0.12		mCPPy2PO (10%)		560		14.8	0.44, 0.54		[35]
3		520^a/552^c		63^a/54^c		140^c		0.16		mCPPy2PO (10%)		564		11.6	0.46, 0.52		[35]
4		566^a/606^c		63^a/64^c		579^c		0.28		mCPPy2PO (10%)		616		10.4	0.61, 0.38		[35]
1		588^a/628^c		84^a/55^c		82.1^c		0.10		mCPPy2PO (10%)		644		15.1	0.64, 0.36		[35]
5		678^a/618^c		12^a/33^c		2.4^c		0.08		mCPPy2PO (10%)		624		10.1	0.60, 0.40		[35]
6		531^a/560^c		88^a/61^c		130^c		0.12		mCPPy2PO (10%)		596		14.8	0.44, 0.54		[35]
7		618^a/765^b		91^a/2^b		145.8^c		0.23		mCPPy2PO (15%)		689		7.68	0.68, 0.30		[37]
8		640^a/688^c		85^a/72^c		49^c		0.11		CBP (6%)		670		15.0	0.66, 0.34		[36]
9		624^a/615^c		31^a/67^c		6.9^c		0.03		CBP (6%)		630		16.2	0.61, 0.39		[36]
10	613^a/633^c		97^a/85^c		60^c		0.18		CBP (6%)		617		20.0			0.59, 0.41		[36]
11	595^a/561^c		31^a/75^c		9.3^c		0.10		CBP (6%)		585		14.0			0.51, 0.48		[36]
12	602^a		40^b/73^c		—		0.25		CBP (7%)		590		26.3			0.52, 0.46		[38]
13	625^a		37^b/63^c		—		0.10		CBP (7%)		606		19.2			0.57, 0.42		[38]
14	682^a		11^b/22^c		—		0.03		CBP (7%)		634		7.1			0.62, 0.37		[38]
15	585^a		97^c		132.98^c		0.13		Nondoped/CBP (15%)/ CBP:PO-T2T (15%)		680/628/628		5.3/27.4/28.1			0.69, 0.30/0.65, 0.35/0.66, 0.34		[39]
16	674^a/672^c		77.7^a/78.1^c		19.2^c		0.14		mCBP (1%)/mCBP (3%)/ mCBP (6%)		651/671/712		19.3/17.7/15.8			—		[40]
17	576^a		10.5^a/0.76^c		2.30^c		0.16		CBP (20%)		604		—			—		[41]
18	593^a		8.3^a/0.62^c		1.51^c		0.10		CBP (20%)		611		9.1			—		[41]
19	610^a		97.1^a		10.3^a		0.03		CBP (18%)		612		20.1			0.60, 0.40		[42]
20	607^a		16^b/100^c		3.6^c		0.03		Nondoped/CBP (14%)		656/604		2.5/ 25.2			0.65, 0.35/0.57, 0.43		[43]
21	638^a		33^a/95^c		7.4^c		0.04		Nondoped/CBP (14%)		680/624		5.2/ 2.5			0.68, 0.32/0.65, 0.38		[43]
22	622^a		49^a		53.5^c		0.23		CBP (8%)		608		8.0			0.58, 0.40		[44]
23	621^a		66^a		5.6^c		0.10		CBP (8%)		604		16.0			0.58, 0.41		[44]
24	622^a		87^c		3.3^c		0.04		CBP (8%)		604		20.1			0.59, 0.41		[44]
25	639^a/756^b/687^c		17^b/63^c		—		0.14		Nondoped/TPBi (10%)		777/693		2.19/10.19			—		[45]
26	656^a		75^a		—		0.48		Nondoped		838		0.58			—		[46]
27	672^a		73^a		—		0.30		Nondoped		916		0.07			—		[46]
28	716^b		16.3^b		8.12^b		0.19		Nondoped/TPBi (10%)		711/630		3.5/ 15.8			—		[47]
29	777^b		20.3^b		10.4^b		0.33		Nondoped/TPBi (5%)/TPBi (15%)		765/700/657		5.1/14.1/14.1			—		[47]
30	628^a/596^c		95^c		3.1^a/4.2^c		0.06		CBP:TPBi (1.5%)		615		27.5			0.58, 0.41		[48]
31	647^a/6.4^c		77^c		1.2^a/2.8^c		0.05		CBP:TPBi (1.5%)		614		26.3			0.60, 0.40		[48]
32	653^a/623^c		0.06^a/0.65^c		3.4^c		0.07		CBP:TPBi (1.5%)		622		21.8			0.61, 0.38		[49]
33	653^a/618^c		0.09^a/0.72^c		3.7^c		0.08		CBP:TPBi (1.5%)		622		24.7			0.61, 0.38		[49]
34	598^a/606^c/692^b		82^a/90^c/13^b		42.7^c		0.07		Nondoped/CBP (3%)		716/606		1.9/ 31.5			0.69, 0.30/0.58, 0.42		[53]
35	612^a/612^c/710^b		74^a/77^c/7^b		28.2^c		0.08		Nondoped/CBP (3%)		748/616		1.4/ 27.1			0.68, 0.28/0.59, 0.40		[53]
36	606^a/610^c/702^b		83^a/76^c/11^b		50.5^c		0.08		Nondoped/CBP (3%)		734/616		1.4/ 27.5			0.70, 0.29/0.59, 0.41		[53]
37	620^a/630^c/702^b		72^a/73^c/6^b		35.6^c		0.08		Nondoped/CBP (3%)		748/622		1.0/ 25.4			0.70, 0.28/0.59, 0.40		[53]
38	584^a/733^b		21^b		0.8^b		0.23		Nondoped/TPBi (15%)		728/644		3.9/ 14.5			0.69, 0.31/0.62, 0.38		[56]
39	724^b/691^c		31^b/90^c		—		0.07		Nondoped/CBP (50%)		700/660		4.62/ 30.3			0.70, 0.30/0.69, 0.31		[57]
40	556^a/625^b		27.2^a/67.1^b		4.36^a/12.0^b		—		—		—		—			—		[54]
41	620^a/644^b		81.3^a87.2^b		4.65^a/5.03^b		0.10		Nondoped (HTL:NPB) Nondoped (HTL:TAPC) Nondoped (HTL:mCP) Nondoped (HTL:TCTA)		636 637 654 652		3.27±0.27 6.30±0.70 10.6±0.95 12.3±1.0			0.65, 0.35 0.66, 0.34 0.66, 0.34 0.67, 0.33		[54]
42	583^a/576^c		90^a/65^c		107.1^c		0.11		Bepp₂ (10%)		676		18.3			0.67, 0.32		[55]
43	613^a/725^b		21^b/87^c		1.96^b		0.23		CBP (10%)		664		20.2			0.68, 0.32		[58]
44	599^a/601^c		43^a/78^c		1.59^c		0.16		mCBP (10%)		596		22.62			0.54, 0.46		[59]
45	675^a/649^c		10^a/12^c		1.15^c		0.02		mCBP (10%)		648		3.52			0.66, 0.34		[59]
46	638^a/640^c		56^a/89^c		0.88^c		0.05		mCBP (10%)		640		26.26			0.62, 0.37		[59]
47	726^a/689^c		12^a/14^c		0.94^c		0.02		mCBP (10%)		684		3.13			0.67, 0.31		[59]

Emitter		λ_PL/nm		Φ_PL/%		τ_DF/μs		ΔE_ST/eV		Host (emitter, w)		λ_EL/nm		EQE/%	CIE (x, y)		Ref
1		588^a/708^b		84^a/14^b		0.76^b		0.13		Nondoped/TPBi (20%)		710/668		2.1/9.8	0.70, 0.29/0.68, 0.32		[34]
2		531^a/560^c		88^a/61^c		130^c		0.12		mCPPy2PO (10%)		560		14.8	0.44, 0.54		[35]
3		520^a/552^c		63^a/54^c		140^c		0.16		mCPPy2PO (10%)		564		11.6	0.46, 0.52		[35]
4		566^a/606^c		63^a/64^c		579^c		0.28		mCPPy2PO (10%)		616		10.4	0.61, 0.38		[35]
1		588^a/628^c		84^a/55^c		82.1^c		0.10		mCPPy2PO (10%)		644		15.1	0.64, 0.36		[35]
5		678^a/618^c		12^a/33^c		2.4^c		0.08		mCPPy2PO (10%)		624		10.1	0.60, 0.40		[35]
6		531^a/560^c		88^a/61^c		130^c		0.12		mCPPy2PO (10%)		596		14.8	0.44, 0.54		[35]
7		618^a/765^b		91^a/2^b		145.8^c		0.23		mCPPy2PO (15%)		689		7.68	0.68, 0.30		[37]
8		640^a/688^c		85^a/72^c		49^c		0.11		CBP (6%)		670		15.0	0.66, 0.34		[36]
9		624^a/615^c		31^a/67^c		6.9^c		0.03		CBP (6%)		630		16.2	0.61, 0.39		[36]
10	613^a/633^c		97^a/85^c		60^c		0.18		CBP (6%)		617		20.0			0.59, 0.41		[36]
11	595^a/561^c		31^a/75^c		9.3^c		0.10		CBP (6%)		585		14.0			0.51, 0.48		[36]
12	602^a		40^b/73^c		—		0.25		CBP (7%)		590		26.3			0.52, 0.46		[38]
13	625^a		37^b/63^c		—		0.10		CBP (7%)		606		19.2			0.57, 0.42		[38]
14	682^a		11^b/22^c		—		0.03		CBP (7%)		634		7.1			0.62, 0.37		[38]
15	585^a		97^c		132.98^c		0.13		Nondoped/CBP (15%)/ CBP:PO-T2T (15%)		680/628/628		5.3/27.4/28.1			0.69, 0.30/0.65, 0.35/0.66, 0.34		[39]
16	674^a/672^c		77.7^a/78.1^c		19.2^c		0.14		mCBP (1%)/mCBP (3%)/ mCBP (6%)		651/671/712		19.3/17.7/15.8			—		[40]
17	576^a		10.5^a/0.76^c		2.30^c		0.16		CBP (20%)		604		—			—		[41]
18	593^a		8.3^a/0.62^c		1.51^c		0.10		CBP (20%)		611		9.1			—		[41]
19	610^a		97.1^a		10.3^a		0.03		CBP (18%)		612		20.1			0.60, 0.40		[42]
20	607^a		16^b/100^c		3.6^c		0.03		Nondoped/CBP (14%)		656/604		2.5/ 25.2			0.65, 0.35/0.57, 0.43		[43]
21	638^a		33^a/95^c		7.4^c		0.04		Nondoped/CBP (14%)		680/624		5.2/ 2.5			0.68, 0.32/0.65, 0.38		[43]
22	622^a		49^a		53.5^c		0.23		CBP (8%)		608		8.0			0.58, 0.40		[44]
23	621^a		66^a		5.6^c		0.10		CBP (8%)		604		16.0			0.58, 0.41		[44]
24	622^a		87^c		3.3^c		0.04		CBP (8%)		604		20.1			0.59, 0.41		[44]
25	639^a/756^b/687^c		17^b/63^c		—		0.14		Nondoped/TPBi (10%)		777/693		2.19/10.19			—		[45]
26	656^a		75^a		—		0.48		Nondoped		838		0.58			—		[46]
27	672^a		73^a		—		0.30		Nondoped		916		0.07			—		[46]
28	716^b		16.3^b		8.12^b		0.19		Nondoped/TPBi (10%)		711/630		3.5/ 15.8			—		[47]
29	777^b		20.3^b		10.4^b		0.33		Nondoped/TPBi (5%)/TPBi (15%)		765/700/657		5.1/14.1/14.1			—		[47]
30	628^a/596^c		95^c		3.1^a/4.2^c		0.06		CBP:TPBi (1.5%)		615		27.5			0.58, 0.41		[48]
31	647^a/6.4^c		77^c		1.2^a/2.8^c		0.05		CBP:TPBi (1.5%)		614		26.3			0.60, 0.40		[48]
32	653^a/623^c		0.06^a/0.65^c		3.4^c		0.07		CBP:TPBi (1.5%)		622		21.8			0.61, 0.38		[49]
33	653^a/618^c		0.09^a/0.72^c		3.7^c		0.08		CBP:TPBi (1.5%)		622		24.7			0.61, 0.38		[49]
34	598^a/606^c/692^b		82^a/90^c/13^b		42.7^c		0.07		Nondoped/CBP (3%)		716/606		1.9/ 31.5			0.69, 0.30/0.58, 0.42		[53]
35	612^a/612^c/710^b		74^a/77^c/7^b		28.2^c		0.08		Nondoped/CBP (3%)		748/616		1.4/ 27.1			0.68, 0.28/0.59, 0.40		[53]
36	606^a/610^c/702^b		83^a/76^c/11^b		50.5^c		0.08		Nondoped/CBP (3%)		734/616		1.4/ 27.5			0.70, 0.29/0.59, 0.41		[53]
37	620^a/630^c/702^b		72^a/73^c/6^b		35.6^c		0.08		Nondoped/CBP (3%)		748/622		1.0/ 25.4			0.70, 0.28/0.59, 0.40		[53]
38	584^a/733^b		21^b		0.8^b		0.23		Nondoped/TPBi (15%)		728/644		3.9/ 14.5			0.69, 0.31/0.62, 0.38		[56]
39	724^b/691^c		31^b/90^c		—		0.07		Nondoped/CBP (50%)		700/660		4.62/ 30.3			0.70, 0.30/0.69, 0.31		[57]
40	556^a/625^b		27.2^a/67.1^b		4.36^a/12.0^b		—		—		—		—			—		[54]
41	620^a/644^b		81.3^a87.2^b		4.65^a/5.03^b		0.10		Nondoped (HTL:NPB) Nondoped (HTL:TAPC) Nondoped (HTL:mCP) Nondoped (HTL:TCTA)		636 637 654 652		3.27±0.27 6.30±0.70 10.6±0.95 12.3±1.0			0.65, 0.35 0.66, 0.34 0.66, 0.34 0.67, 0.33		[54]
42	583^a/576^c		90^a/65^c		107.1^c		0.11		Bepp₂ (10%)		676		18.3			0.67, 0.32		[55]
43	613^a/725^b		21^b/87^c		1.96^b		0.23		CBP (10%)		664		20.2			0.68, 0.32		[58]
44	599^a/601^c		43^a/78^c		1.59^c		0.16		mCBP (10%)		596		22.62			0.54, 0.46		[59]
45	675^a/649^c		10^a/12^c		1.15^c		0.02		mCBP (10%)		648		3.52			0.66, 0.34		[59]
46	638^a/640^c		56^a/89^c		0.88^c		0.05		mCBP (10%)		640		26.26			0.62, 0.37		[59]
47	726^a/689^c		12^a/14^c		0.94^c		0.02		mCBP (10%)		684		3.13			0.67, 0.31		[59]

喹喔啉类红光热活化延迟荧光材料研究进展

Research Progress of Red Thermally Activated Delayed Fluorescent Materials Based on Quinoxaline

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